Acetyl chloride → N-(5,6-dichloropyridin-3-yl)acetamide

HRID 1259138Notes

Reaction equation

HRID 1259138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[N:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:17](=[O:19])[CH3:18])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 145952195-Amino-2,3-dichloropyridine

Product 1

HCID 86652352N-(5,6-dichloropyridin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5,6-dichloropyridin-3-amine (commercially available) and triethyl amine (3 eq) in CH2Cl2 (0.2 M) at 0° C. was added acetyl chloride (2 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford N-(5,6-dichloropyridin-3-yl)acetamide.

Workup

  1. concentrationwas concentrated under vacuum
  2. customthe resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-86fe29c5dd154d17ae1e7c5347ad4677
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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